Multi-step reaction with 7 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 5 h / 20 °C / Inert atmosphere
2.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.08 h / -78 °C / Inert atmosphere
2.2: 0.17 h / -78 °C / Inert atmosphere
2.3: -78 °C / Inert atmosphere
3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 23 h / 20 °C / Inert atmosphere
4.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran; hexane / 0.05 h / -98 °C / Inert atmosphere
4.2: 2 h / -98 - -60 °C / Inert atmosphere
4.3: Inert atmosphere
5.1: 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; tert-butylmagnesium chloride / tetrahydrofuran; dichloromethane / 20 °C / Inert atmosphere
5.2: 20 °C / Inert atmosphere
6.1: diisopropyl-carbodiimide / dichloromethane / 24 h / 20 °C / Inert atmosphere
7.1: titanium(IV) isopropylate; n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - 50 °C / Inert atmosphere
7.2: Inert atmosphere
With
titanium(IV) isopropylate; n-butyllithium; 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; N,N,N,N,-tetramethylethylenediamine; tert-butylmagnesium chloride; tert.-butyl lithium; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; pentane;
DOI:10.1021/ol300276p